Structure of 20577-27-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 20577-27-9 |
Formula : | C6H4N2O |
M.W : | 120.11 |
SMILES Code : | O=C1C(=CC=CN1)C#N |
MDL No. : | MFCD00661865 |
InChI Key : | DYUMBFTYRJMAFK-UHFFFAOYSA-N |
Pubchem ID : | 577543 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H318 |
Precautionary Statements: | P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 31.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
56.65 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.88 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.13 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.47 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.16 |
Solubility | 8.31 mg/ml ; 0.0692 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.88 |
Solubility | 16.0 mg/ml ; 0.133 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.97 |
Solubility | 1.29 mg/ml ; 0.0107 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.94 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.52 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Acetic acid (34 ml) was added to 2-oxo-1,2-dihydropyridine-3-carbonitrile (6.28 g, 0.052 mol) and the mixture was heated to 130C. When the solid was dissolved, bromine (12.5 g, 0.078 mol) was added slowly and stirred at the same temperature for 3 hours.After the reaction solution was cooled to room temperature, dichloromethane and water were added. The organic layer was separated and the aqueous layer was washed with dichloromethane. The organic layer was collected, washed with brine, dried over anhydrous sodium sulfate and concentrated to give the desired compound (9.11 g, 88% yield) as a yellow solid. | |
75% | With bromine; sodium acetate; In acetic acid; at 20.0℃; for 2.0h; | 5-Bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile(12) To a stirring solutionof compound 11 (50 mg, 0.42 mmol)and NaOAc (69 mg, 0.84 mmol) in 5 mL glacial AcOH at room temperature was addedBr2 (21.5 muL, 0.42 mmol) for 2 h. The mixture was concentrated invacuum to remove AcOH. Purification by chromatography (EA) provided compound 12 (69 mg, 75%) as a yellow solid. MP:216~217C. 1H NMR (400 MHz, CD3COCD3): delta 11.70 (s, 1H), 8.22 (d, J= 2.8 Hz, 1H), 8.05 (d, J = 2.8 Hz, 1H).5 |
With bromine; In acetic acid; at 20.0℃; for 14.0h; | 5-Bromo-2-oxo-1,2-dihydro-pyridine-3-carbonitrile Brornine (29 ml, 560 mmol) was added to a stirred solution of 2-oxo-1,2-dihydro-pyridine-3-carbonitrile (34 g, 280 mmol) in acetic acid (180 ml) at room temperature. After 14 hours the reaction mixture was concentrated in vacuo and the resulting oil was trituated with ethanol to afford the title compound as a solid. 1H NMR delta (d6 DMSO) 12.8 (brs, 1H), 8.4 (d, 1H), 8.1 (d, 1H). |
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